Bis(1H-benz­imidazole-κN³)(oxy­diacetato-κ³O,O′,O′′)­zinc(II)

In the title compound, [Zn(C₇H₆N₂)₂(C₄H₄O₅)], one oxydi­acetate dianion and two benz­imidazole mol­ecules coordinate to the Zn^II atom in distorted trigonal-bipyramidal coordination geometry. The interplanar distance of 3.422 (4) Å between parallel benz­imidazole rings of neighbouring mol­ecules indicates the existence of π–π stacking.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.027
• wR factor = 0.070
• Data-to-parameter ratio = 12.4

checkCIF/PLATON results

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Alert level C
PLAT301_ALERT_3_C Main Residue  Disorder .........................       3.00 Perc.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: PROCESS-AUTO (Rigaku Corporation, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and XP (Siemens, 1994); software used to prepare material for publication: WinGX (Farrugia, 1999).

Bis(1H-benzimidazole-κN³)(oxydiacetato-κ³O,O',O'')zinc(II)

Crystal data

[Zn(C7H6N2)2(C4H4O5)]	F(000) = 1776
Mr = 433.72	Dx = 1.598 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 6382 reflections
a = 25.049 (6) Å	θ = 2.4–25.5°
b = 7.0568 (18) Å	µ = 1.40 mm^−1
c = 21.420 (5) Å	T = 295 K
β = 107.783 (3)°	Prism, colourless
V = 3605.4 (15) Å^3	0.32 × 0.28 × 0.22 mm
Z = 8

Data collection

Rigaku R-AXIS RAPID diffractometer	3258 independent reflections
Radiation source: fine-focus sealed tube	2883 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
Detector resolution: 10.00 pixels mm^-1	θmax = 25.2°, θmin = 1.7°
ω scans	h = −30→17
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −8→8
Tmin = 0.648, Tmax = 0.737	l = −25→25
7413 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.070	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0367P)^2 + 2.2003P] where P = (Fo^2 + 2Fc^2)/3
3258 reflections	(Δ/σ)max = 0.001
262 parameters	Δρmax = 0.27 e Å^−3
0 restraints	Δρmin = −0.27 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Zn	0.363701 (9)	0.02472 (3)	0.134771 (11)	0.03246 (9)
O1	0.39367 (7)	0.2767 (2)	0.17818 (7)	0.0493 (4)
O2	0.41049 (8)	0.4574 (2)	0.26737 (8)	0.0598 (5)
O3A	0.3535 (3)	0.0040 (11)	0.2281 (4)	0.0480 (18)	0.42
O3B	0.3308 (2)	0.0459 (9)	0.2140 (3)	0.0425 (12)	0.58
O4	0.31510 (6)	−0.2170 (2)	0.13018 (6)	0.0399 (3)
O5	0.26946 (7)	−0.4015 (2)	0.18119 (7)	0.0470 (4)
N11	0.50045 (8)	−0.3332 (3)	0.15737 (9)	0.0497 (5)
H11	0.5168	−0.4401	0.1695	0.060*
N13	0.43682 (7)	−0.1073 (2)	0.14148 (8)	0.0380 (4)
N21	0.27846 (7)	0.0731 (3)	−0.06353 (9)	0.0394 (4)
H21	0.2579	0.0212	−0.0991	0.047*
N23	0.32499 (7)	0.1079 (2)	0.04178 (8)	0.0325 (4)
C1	0.39004 (9)	0.3166 (3)	0.23424 (10)	0.0409 (5)
C2	0.35733 (12)	0.1822 (3)	0.26321 (11)	0.0564 (7)
H2A	0.3763	0.1638	0.3096	0.068*	0.42
H2B	0.3202	0.2324	0.2581	0.068*	0.42
H2C	0.3814	0.1327	0.3045	0.068*	0.58
H2D	0.3260	0.2472	0.2714	0.068*	0.58
C3	0.31420 (10)	−0.1310 (3)	0.23705 (10)	0.0454 (5)
H3A	0.2812	−0.0669	0.2411	0.055*	0.42
H3B	0.3307	−0.2037	0.2767	0.055*	0.42
H3C	0.2813	−0.0974	0.2495	0.055*	0.58
H3D	0.3410	−0.1924	0.2740	0.055*	0.58
C4	0.29830 (8)	−0.2607 (3)	0.17813 (9)	0.0337 (4)
C12	0.45212 (9)	−0.2774 (3)	0.16551 (10)	0.0442 (5)
H12	0.4315	−0.3508	0.1859	0.053*
C14	0.48670 (9)	0.1244 (3)	0.08802 (11)	0.0460 (5)
H14	0.4609	0.2226	0.0827	0.055*
C15	0.53354 (10)	0.1421 (4)	0.06749 (12)	0.0555 (6)
H15	0.5396	0.2552	0.0484	0.067*
C16	0.57183 (11)	−0.0041 (4)	0.07461 (14)	0.0576 (7)
H16	0.6023	0.0123	0.0589	0.069*
C17	0.56624 (9)	−0.1727 (4)	0.10418 (12)	0.0534 (6)
H17	0.5922	−0.2701	0.1092	0.064*
C18	0.51949 (9)	−0.1896 (3)	0.12618 (10)	0.0407 (5)
C19	0.47949 (8)	−0.0463 (3)	0.11704 (10)	0.0370 (5)
C22	0.29323 (8)	−0.0037 (3)	−0.00387 (11)	0.0374 (5)
H22	0.2822	−0.1242	0.0047	0.045*
C24	0.35998 (9)	0.4402 (3)	0.03192 (11)	0.0380 (5)
H24	0.3788	0.4575	0.0762	0.046*
C25	0.35913 (10)	0.5794 (3)	−0.01365 (11)	0.0456 (5)
H25	0.3784	0.6921	0.0003	0.055*
C26	0.33023 (10)	0.5555 (3)	−0.07988 (12)	0.0489 (6)
H26	0.3307	0.6527	−0.1090	0.059*
C27	0.30112 (10)	0.3929 (3)	−0.10336 (11)	0.0451 (5)
H27	0.2816	0.3779	−0.1476	0.054*
C28	0.30224 (8)	0.2511 (3)	−0.05779 (10)	0.0337 (4)
C29	0.33146 (8)	0.2731 (3)	0.00873 (9)	0.0303 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn	0.03580 (15)	0.03087 (14)	0.03296 (14)	−0.00427 (10)	0.01386 (10)	−0.00040 (9)
O1	0.0679 (10)	0.0391 (9)	0.0444 (9)	−0.0189 (8)	0.0227 (8)	−0.0066 (7)
O2	0.0767 (12)	0.0445 (9)	0.0515 (10)	−0.0274 (9)	0.0098 (9)	−0.0135 (8)
O3A	0.072 (5)	0.036 (4)	0.044 (4)	−0.029 (3)	0.031 (4)	−0.014 (3)
O3B	0.059 (3)	0.038 (3)	0.036 (2)	−0.020 (2)	0.022 (2)	−0.0109 (17)
O4	0.0496 (9)	0.0368 (8)	0.0367 (8)	−0.0138 (7)	0.0182 (7)	−0.0059 (6)
O5	0.0569 (10)	0.0434 (9)	0.0413 (8)	−0.0222 (8)	0.0161 (7)	−0.0022 (7)
N11	0.0481 (11)	0.0379 (10)	0.0562 (12)	0.0097 (9)	0.0056 (9)	0.0104 (9)
N13	0.0361 (9)	0.0355 (9)	0.0419 (10)	0.0009 (8)	0.0114 (8)	0.0051 (8)
N21	0.0357 (9)	0.0414 (10)	0.0375 (10)	−0.0015 (8)	0.0057 (7)	−0.0079 (8)
N23	0.0343 (9)	0.0285 (8)	0.0349 (9)	−0.0022 (7)	0.0106 (7)	−0.0004 (7)
C1	0.0467 (12)	0.0346 (11)	0.0364 (11)	−0.0085 (9)	0.0051 (9)	−0.0016 (9)
C2	0.0846 (18)	0.0468 (14)	0.0412 (12)	−0.0279 (13)	0.0243 (12)	−0.0187 (10)
C3	0.0619 (14)	0.0429 (13)	0.0365 (11)	−0.0223 (11)	0.0225 (10)	−0.0049 (9)
C4	0.0325 (10)	0.0333 (11)	0.0344 (10)	−0.0035 (9)	0.0088 (8)	0.0023 (8)
C12	0.0459 (13)	0.0402 (12)	0.0429 (12)	−0.0025 (10)	0.0079 (10)	0.0086 (10)
C14	0.0419 (12)	0.0405 (12)	0.0572 (14)	0.0045 (10)	0.0176 (11)	0.0102 (10)
C15	0.0477 (14)	0.0575 (16)	0.0648 (16)	−0.0056 (12)	0.0224 (12)	0.0103 (12)
C16	0.0417 (13)	0.0703 (18)	0.0664 (17)	−0.0040 (12)	0.0248 (12)	−0.0021 (13)
C17	0.0341 (12)	0.0617 (16)	0.0616 (15)	0.0097 (11)	0.0104 (11)	−0.0087 (12)
C18	0.0362 (11)	0.0380 (12)	0.0424 (12)	0.0040 (9)	0.0039 (9)	0.0012 (9)
C19	0.0320 (10)	0.0392 (11)	0.0384 (11)	0.0009 (9)	0.0086 (9)	0.0016 (9)
C22	0.0348 (11)	0.0317 (11)	0.0471 (12)	−0.0027 (9)	0.0145 (9)	−0.0023 (9)
C24	0.0413 (12)	0.0311 (11)	0.0404 (11)	−0.0013 (9)	0.0108 (9)	−0.0011 (9)
C25	0.0507 (13)	0.0327 (11)	0.0568 (14)	−0.0008 (10)	0.0213 (11)	0.0027 (10)
C26	0.0568 (14)	0.0404 (13)	0.0554 (15)	0.0102 (11)	0.0256 (12)	0.0167 (11)
C27	0.0485 (13)	0.0516 (14)	0.0352 (11)	0.0154 (11)	0.0128 (10)	0.0070 (10)
C28	0.0292 (10)	0.0353 (11)	0.0376 (10)	0.0056 (8)	0.0119 (8)	−0.0015 (9)
C29	0.0278 (10)	0.0291 (10)	0.0353 (10)	0.0038 (8)	0.0114 (8)	0.0003 (8)

Geometric parameters (Å, º)

Zn—N13	2.0205 (18)	C2—H2C	0.9700
Zn—N23	2.0181 (16)	C2—H2D	0.9700
Zn—O1	2.0406 (15)	C3—H3A	0.9700
Zn—O3A	2.098 (9)	C3—H3B	0.9700
Zn—O3B	2.105 (6)	C3—H3C	0.9700
Zn—O4	2.0807 (14)	C3—H3D	0.9700
O1—C1	1.264 (2)	C12—H12	0.9300
O2—C1	1.237 (2)	C14—C15	1.379 (3)
O3A—C2	1.453 (9)	C14—C19	1.393 (3)
O3A—C3	1.424 (9)	C14—H14	0.9300
O3B—C2	1.433 (7)	C15—C16	1.385 (4)
O3B—C3	1.449 (7)	C15—H15	0.9300
C1—C2	1.505 (3)	C16—C17	1.375 (4)
C3—C4	1.511 (3)	C16—H16	0.9300
O4—C4	1.261 (2)	C17—C18	1.394 (3)
O5—C4	1.241 (2)	C17—H17	0.9300
N11—C12	1.334 (3)	C18—C19	1.395 (3)
N11—C18	1.377 (3)	C22—H22	0.9300
N11—H11	0.8600	C24—C25	1.381 (3)
N13—C12	1.316 (3)	C24—C29	1.389 (3)
N13—C19	1.394 (3)	C24—H24	0.9300
N21—C22	1.332 (3)	C25—C26	1.392 (3)
N21—C28	1.380 (3)	C25—H25	0.9300
N21—H21	0.8600	C26—C27	1.371 (3)
N23—C22	1.317 (3)	C26—H26	0.9300
N23—C29	1.399 (2)	C27—C28	1.392 (3)
C2—H2A	0.9700	C27—H27	0.9300
C2—H2B	0.9700	C28—C29	1.397 (3)
N23—Zn—N13	110.87 (7)	O3B—C2—C1	107.9 (3)
N23—Zn—O1	101.26 (6)	O3B—C3—C4	105.5 (3)
N13—Zn—O1	99.80 (7)	O3B—C2—H2C	116.6
N23—Zn—O4	95.40 (6)	O3B—C2—H2D	103.4
N13—Zn—O4	97.45 (7)	O3B—C3—H3C	103.9
O1—Zn—O4	149.84 (6)	O3B—C3—H3D	117.6
N23—Zn—O3A	143.09 (18)	H3A—C3—H3B	108.4
N13—Zn—O3A	105.79 (18)	H3C—C3—H3D	108.7
O1—Zn—O3A	76.2 (2)	O5—C4—O4	125.64 (19)
O4—Zn—O3A	75.4 (2)	O5—C4—C3	116.75 (17)
N23—Zn—O3B	125.90 (12)	O4—C4—C3	117.61 (17)
N13—Zn—O3B	123.00 (12)	N13—C12—N11	112.7 (2)
O1—Zn—O3B	75.59 (18)	N13—C12—H12	123.7
O4—Zn—O3B	74.27 (18)	N11—C12—H12	123.7
C1—O1—Zn	120.27 (13)	C15—C14—C19	117.4 (2)
C3—O3A—C2	116.7 (6)	C15—C14—H14	121.3
C3—O3A—Zn	117.7 (5)	C19—C14—H14	121.3
C2—O3A—Zn	115.1 (5)	C14—C15—C16	121.7 (2)
C2—O3B—C3	116.4 (4)	C14—C15—H15	119.2
C2—O3B—Zn	115.7 (4)	C16—C15—H15	119.2
C3—O3B—Zn	116.0 (4)	C17—C16—C15	122.1 (2)
C4—O4—Zn	119.86 (12)	C17—C16—H16	119.0
C12—N11—C18	107.99 (18)	C15—C16—H16	119.0
C12—N11—H11	126.0	C16—C17—C18	116.4 (2)
C18—N11—H11	126.0	C16—C17—H17	121.8
C12—N13—C19	105.27 (18)	C18—C17—H17	121.8
C12—N13—Zn	126.72 (15)	N11—C18—C17	132.7 (2)
C19—N13—Zn	127.81 (14)	N11—C18—C19	105.16 (19)
C22—N21—C28	107.39 (17)	C17—C18—C19	122.1 (2)
C22—N21—H21	126.3	C14—C19—C18	120.3 (2)
C28—N21—H21	126.3	C14—C19—N13	130.82 (19)
C22—N23—C29	105.05 (16)	C18—C19—N13	108.87 (18)
C22—N23—Zn	123.92 (14)	N23—C22—N21	113.38 (18)
C29—N23—Zn	130.32 (13)	N23—C22—H22	123.3
O2—C1—O1	125.9 (2)	N21—C22—H22	123.3
O2—C1—C2	116.8 (2)	C25—C24—C29	117.1 (2)
O1—C1—C2	117.23 (18)	C25—C24—H24	121.4
C1—C2—H2A	110.3	C29—C24—H24	121.4
C1—C2—H2B	110.3	C24—C25—C26	121.7 (2)
C1—C2—H2C	109.8	C24—C25—H25	119.2
C1—C2—H2D	110.4	C26—C25—H25	119.2
C4—C3—H3A	110.1	C27—C26—C25	121.9 (2)
C4—C3—H3B	110.1	C27—C26—H26	119.1
C4—C3—H3C	110.3	C25—C26—H26	119.1
C4—C3—H3D	110.6	C26—C27—C28	116.8 (2)
O3A—C2—C1	106.9 (4)	C26—C27—H27	121.6
O3A—C3—C4	108.1 (4)	C28—C27—H27	121.6
O3A—C2—H2A	110.3	N21—C28—C27	132.5 (2)
O3A—C2—H2B	110.3	N21—C28—C29	105.63 (17)
O3A—C3—H3A	110.1	C27—C28—C29	121.82 (19)
O3A—C3—H3B	110.1	C24—C29—C28	120.72 (18)
H2A—C2—H2B	108.6	C24—C29—N23	130.74 (18)
H2C—C2—H2D	108.4	C28—C29—N23	108.54 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···O2^i	0.86	2.04	2.750 (3)	139
N21—H21···O5^ii	0.86	1.88	2.722 (2)	165

Symmetry codes: (i) −x+1, y−1, −z+1/2; (ii) −x+1/2, −y−1/2, −z.